Trifluoroacetic acid → HCID 131715529, compound

HRID 1252625Notes

Reaction equation

HRID 1252625 reaction equation
[OH:1][C:2]1[C:3](=[O:42])[CH:4]=[C:5]([C:8]([N:10]([CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[NH:11][S:12]([NH:15][C:16]([N:18]2[CH2:21][C@H:20]([NH:22]C(OCC3C=CC=CC=3)=O)[C:19]2=[O:33])=[O:17])(=[O:14])=[O:13])=[O:9])[NH:6][CH:7]=1.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].C1(SC)C=CC=CC=1>>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[NH2:22][C@H:20]1[CH2:21][N:18]([C:16]([NH:15][S:12]([NH:11][N:10]([CH2:34][C:35]([OH:37])=[O:36])[C:8]([C:5]2[NH:6][CH:7]=[C:2]([OH:1])[C:3](=[O:42])[CH:4]=2)=[O:9])(=[O:13])=[O:14])=[O:17])[C:19]1=[O:33]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 131715530HCID 131715530, compound

Product 1

HCID 131715529HCID 131715529, compound

Procedure

At 0° C., 2.39 g (3.9 mmol) of (3S)-[1-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]-2-[[[[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]carbonyl]amino]sulfonyl]hydrazino]acetic acid, 1,1-dimethylethyl ester was added to a mixture of 7.0 ml of trifluoroacetic acid and 1.66 ml of thioanisole. After stirring overnight at room temperature, the solution was evaporated in vacuo. The residue was successively washed (stirred) with ethyl acetate, ethyl acetate/petroleum ether (1:1), petroleum ether and dichloromethane and then dried in vacuo. This crude salt was used in the next step without any further purification. Yield: 2.15 g.

Workup

  1. customthe solution was evaporated in vacuo
  2. washThe residue was successively washed
  3. stirring(stirred) with ethyl acetate, ethyl acetate/petroleum ether (1:1), petroleum ether and dichloromethane
  4. customdried in vacuo
  5. customThis crude salt was used in the next step without any further purification

Sources & evidence

ORD record
ord-e2853c7439724abd90276865a5b8e314
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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